2-chloro-1-(4'-methanesulfonamidophenyl)ethanol | 187831-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-1-(4'-methanesulfonamidophenyl)ethanol
• 英文别名: N-{4-[(1S)-2-chloro-1-hydroxyethyl]phenyl}methanesulfonamide；N-[4-[(1S)-2-chloro-1-hydroxyethyl]phenyl]methanesulfonamide
• CAS: 187831-22-7
• 化学式: C₉H₁₂ClNO₃S
• mdl: MFCD09863636
• 分子量: 249.718
• InChiKey: UMJVCKLQCMEZSH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[4-(2-氯乙酰基)苯基]甲磺酰胺 在 chloro[(1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine] (pentamethylcyclopentadienyl) rhodium 甲酸 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以80%的产率得到2-chloro-1-(4'-methanesulfonamidophenyl)ethanol
  参考文献：
  名称：

  通过手性铑-二胺催化剂对α-氯代酮的不对称转移加氢，可以实际合成旋光性芳族环氧化物

  摘要：

  通过形成光学活性的α-氯化醇和分子内醚化，已经开发了一种合成光学活性的芳族环氧化物的实用方法。使用含有明确定义的手性Rh络合物Cp * RhCl [（[R， [R）-Tsdpen]。由于二胺基Cp * Rh（III）氢化物配合物的配位饱和特性，用手性Rh催化剂不对称还原α-氯化芳族酮的特征是快速且羰基选择性转化。还原的结果受酮底物的结构以及氢源（如甲酸或2-丙醇）的影响很大。无需特殊纯化即可在该反应中使用市售的试剂和溶剂。一锅法或两锅法的这种环氧化物合成方法是实用的，对于从α-氯代酮大规模生产旋光性苯乙烯氧化物特别有用。

  DOI：

  10.1016/j.tet.2004.06.076

文献信息

• Practical Synthesis of Optically Active Styrene Oxides via Reductive Transformation of 2-Chloroacetophenones with Chiral Rhodium Catalysts
  作者：Takayuki Hamada、Takayoshi Torii、Kunisuke Izawa、Ryoji Noyori、Takao Ikariya

  DOI：10.1021/ol020213o

  日期：2002.11.1

  [reaction: see text] A practical method for the synthesis of optically active styrene oxides has been developed via formation of optically active 2-chloro-1-phenylethanols generated by reductive transformation of ring-substituted 2-chloroacetophenones. The optically active alcohols with up to 98% ee are obtainable from the asymmetric reduction of acetophenones with an S/C = 1000-5000 with a formic

  [反应：见正文]通过形成由环取代的2-氯苯乙酮的还原转化而生成的光学活性的2-氯-1-苯基乙醇，已经开发了一种合成光学活性的苯乙烯氧化物的实用方法。ee高达98％的旋光性醇可通过将S / C = 1000-5000的苯乙酮与含有明确定义的手性Rh络合物CpRhCl [（R，R）- tsdpen]。
• A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium–diamine catalyst
  作者：Takayuki Hamada、Takayoshi Torii、Kunisuke Izawa、Takao Ikariya

  DOI：10.1016/j.tet.2004.06.076

  日期：2004.8

  A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from the asymmetric reduction of aromatic ketones with a substrate/catalyst ratio of 1000–5000 using a formic acid/triethylamine mixture containing a well-defined

  通过形成光学活性的α-氯化醇和分子内醚化，已经开发了一种合成光学活性的芳族环氧化物的实用方法。使用含有明确定义的手性Rh络合物Cp * RhCl [（[R， [R）-Tsdpen]。由于二胺基Cp * Rh（III）氢化物配合物的配位饱和特性，用手性Rh催化剂不对称还原α-氯化芳族酮的特征是快速且羰基选择性转化。还原的结果受酮底物的结构以及氢源（如甲酸或2-丙醇）的影响很大。无需特殊纯化即可在该反应中使用市售的试剂和溶剂。一锅法或两锅法的这种环氧化物合成方法是实用的，对于从α-氯代酮大规模生产旋光性苯乙烯氧化物特别有用。
• anti-Prelog microbial reduction of aryl α-halomethyl or α-hydroxymethyl ketones with Geotrichum sp. 38
  作者：Zhi-Liang Wei、Zu-Yi Li、Guo-Qiang Lin

  DOI：10.1016/s0040-4020(98)00796-0

  日期：1998.10

  Reduction of aryl α-halomethyl ketones 5a-d and 7a-h and α-hydroxymethyl ketones 10a-b by Geotrichum sp. 38 affording mostly the anti-Prelog alcohols was reported and the stereoselectivities of the reductive products were discussed.

  芳基α-卤代甲基酮的还原图5a-d以及图7a-H和α羟基酮10A-B由白地霉属。报道了38种主要提供抗-Prelog醇的化合物，并讨论了还原产物的立体选择性。
• Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol
  作者：Ahmed Kamal、Mahendra Sandbhor、Ahmad Ali Shaik

  DOI：10.1016/j.bmcl.2004.05.084

  日期：2004.9

  Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantio selectivity under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.
• Biocatalytic synthesis of some chiral drug intermediates by oxidoreductases
  作者：Ramesh N. Patel、Ronald L. Hanson、Amit Banerjee、Laszlo J. Szarka

  DOI：10.1007/s11746-997-0237-3

  日期：1997.11

  AbstractChiral intermediates were prepared by biocatalytic processes with oxidoreductases for the chemical synthesis of some pharmaceutical drug candidates. These include: (i) the microbial reduction of 1‐(4‐fluorophenyl)‐4‐[4‐(5‐fluoro‐2‐pyrimidinyl)‐1‐piperazinyl]‐1‐butanone (1) to R‐(+)‐1‐(4‐fluorophenyl)‐4‐[4‐(5‐fluoro‐2‐pyrimidinyl)‐1‐piperazinyl]‐1‐butanol (2) [R‐(+)‐BMY 14802], an antipsychotic agent; (ii) the reduction of N‐4‐(1‐oxo‐2‐chloroacetyl ethyl) phenyl methane sulfonamide (3) to the corresponding chiral alcohol (4), an intermediate for d‐(+)‐N‐4‐1‐hydroxy‐2‐[(‐methylethyl)amino]ethyl}phenyl methanesulfonamide [d‐(+) sotalol], a β‐blocker with class III antiarrhythmic properties; (iii) biotransformation of Nɛ‐carbobenzoxy (CBZ)‐l‐lysine (7) to Nɛ‐CBZ‐l‐oxylysine (5), an intermediate needed for synthesis of (S)‐1‐[6‐amino‐2‐[hydroxy(4‐phenylbutyl)phosphinyl]oxy}1‐oxohexyl]‐l‐proline (ceronapril), a new angiotensin converting enzyme inhibitor (6) and (iv) enzymatic synthesis of l‐β‐hydroxyvaline (9) from α‐keto‐β‐hydroxyisovalerate (16). l‐β‐Hydroxyvaline (9) is a key chiral intermediate needed for the synthesis of S‐(Z)‐[1‐(2‐amino‐4‐thiazolyl)‐2‐[2,2‐dimethyl‐4‐oxo‐1‐(sulfooxy)‐3‐azetidinyl] amino}‐2‐oxoethylidene]amino}oxyacetic acid (tigemonam) (10), an orally active monobactam.